Copper‐Catalyzed Double <i>N</i>‐Vinylation of Aromatic Amines: An Efficient Synthesis of Various Substituted <i>N</i>‐Arylpyrroles

Abstract

Abstract A simple and efficient approach to various substituted N ‐arylpyrroles has been developed. The method is based on the copper‐catalyzed sequential inter‐ and intramolecular N ‐vinylation of aromatic amines. The reactions proceed to afford substituted N ‐arylpyrroles in good‐to‐excellent yields using CuI as the precatalyst, t BuONa as the base, and N 1 , N 2 ‐dimethylethane‐1,2‐diamine (DMEDA) as the ligand. Anilines with electron‐donating and ‐withdrawing substituents as well as a heteroaromatic amine performed very well under the conditions used. Tri‐ and tetrasubstituted dienyl diiodides also performed well under the reaction conditions and afforded the corresponding substituted N ‐arylpyrroles in good yields. Products were also obtained in high yields with CuBr or CuCl as precatalyst.